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Sodium docusate → (E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium docusate

HRID 922002
ノート
印刷プレビュー

反応式

HRID 922002 の反応式
[Cl-].[CH3:2]/[C:3](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:4]\[CH2:5][O:6][C:7](=[O:15])[CH2:8][N:9]1[CH:13]=[CH:12][N+:11]([CH3:14])=[CH:10]1.[Na].[CH3:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:30][O:31][C:32]([CH2:34][CH:35]([S:47]([OH:50])(=[O:49])=[O:48])[C:36]([O:38][CH2:39][CH:40]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:41][CH3:42])=[O:37])=[O:33])[CH2:28][CH3:29]>CC(C)=O.O.O>[CH3:2]/[C:3](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:4]\[CH2:5][O:6][C:7](=[O:15])[CH2:8][N:9]1[CH:13]=[CH:12][N+:11]([CH3:14])=[CH:10]1.[CH3:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:30][O:31][C:32]([CH2:34][CH:35]([S:47]([OH:50])(=[O:49])=[O:48])[C:36]([O:38][CH2:39][CH:40]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:41][CH3:42])=[O:37])=[O:33])[CH2:28][CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 9955175Sodium docusateHCID 86662343(E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium chloride

生成物 1

HCID 86662344(E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium docusate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 18366337Propan-2-one--water (1/1)溶媒

実験手順

Imidazolium chloride [3] (312.8 mg, 1 mmol) and sodium docusate (444.6 mg, 1 mmol) were dissolved in 20 ml of acetone/H2O 1:1 and stirred overnight at room temperature. The remaining suspension was diluted with 50 ml of H2O and extracted with dichloromethane. The organic layer was washed successively with water until no more chloride ions could be detected in the washings (checked by addition of AgNO3 solution), dried over MgSO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to give imidazolium docusate [4] in quantitative yield as yellow oil. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=9.07 (s, 1H), 7.71 (s, 2H), 5.33 (t, J=7.3 Hz, 1H), 5.24 (s, 2H), 5.07 (m, 1H), 4.69 (d, J=7.3 Hz, 2H), 3.91 (s, 3H), 3.90 (m, 4H), 3.62 (dd, J1=11.39 Hz, J2=3.88 Hz, 1H), 2.86 (m, 2H), 2.04 (m, 4H), 1.68 (s, 3H), 1.65 (s, 3H), 1.57 (s, 3H), 1.49 (m, 2H), 1.24 (m, 16 H), 0.84 (m, 12H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=171.1, 168.1, 166.9, 142.7, 137.7, 131.2, 123.7, 123.6, 123.4, 117.6, 66.2, 66.1, 62.4, 61.4, 49.5, 38.1, 356.0, 34.1, 29.8, 29.6, 28.3, 25.8, 25.5, 23.2, 23.0, 22.4, 17.6, 16.2, 13.9, 10.8. T5%onset 170° C.

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed successively with water until no more chloride ions
  3. additioncould be detected in the washings (checked by addition of AgNO3 solution)
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated
  6. customwas removed under reduced pressure (0.01 mbar)

出典と根拠

ORDレコード
ord-aabe74ff181944e0bf32ea01ccdbfd55
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278134B2

反応ノート

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